Molecules 2005, 10(1), 217-225; doi:10.3390/10010217
Article

Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones

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Received: 5 July 2004; Accepted: 14 July 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIBapproach is a useful alternative to analogous sequences in which Tl(NO3)3·3H2O or thePrevost combination (AgNO3/I2) are employed in the oxidation step.
Keywords: [Hydroxy(tosyloxy)iodo]benzene; benzocycloalkenones; ring expansion; oxidative rearrangement
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MDPI and ACS Style

Justik, M.; Koser, G. Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones. Molecules 2005, 10, 217-225.

AMA Style

Justik M, Koser G. Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones. Molecules. 2005; 10(1):217-225.

Chicago/Turabian Style

Justik, M.; Koser, G. 2005. "Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones." Molecules 10, no. 1: 217-225.

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